Sodium Acetate → HCID 14501368, compound

HRID 1904600Notes

Reaction equation

HRID 1904600 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([F:28])=[CH:10][C:11]3[C:21](=[O:22])[C:20]([C:23]([O:25]CC)=[O:24])=[CH:19][N:13]4[C@@H:14]([CH3:18])[CH2:15][O:16][C:17]=2[C:12]=34)[CH:5]=[C:4]([CH3:29])[N:3]=1.C([O-])(=O)C.[Na+]>Cl>[CH3:29][C:4]1[CH:5]=[C:6]([C:8]2[C:9]([F:28])=[CH:10][C:11]3[C:21](=[O:22])[C:20]([C:23]([OH:25])=[O:24])=[CH:19][N:13]4[C@@H:14]([CH3:18])[CH2:15][O:16][C:17]=2[C:12]=34)[CH:7]=[C:2]([CH3:1])[N:3]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 14501365ethyl (S)-10-(2,6-dimethyl-4-pyridinyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate

Product 1

HCID 14501368HCID 14501368, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 0.52 g ethyl (S)-10-(2,6-dimethyl-4-pyridinyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate and 10 ml 1M hydrochloric acid was heated at reflux for one hour. The reaction mixture was cooled, poured into sodium acetate solution and extracted with chloroform. The extract was dried (sodium sulfate) and concentrated, and the residue was recrystallized from methanol to give 300 mg (S)-10-(2,6-dimethyl-4-pyridinyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid, colorless powder, m.p. 305°-308° C., [α]D25 =-39.8°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for one hour
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with chloroform
  5. dry with materialThe extract was dried (sodium sulfate)
  6. concentrationconcentrated
  7. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-32bc50d8004744f1b297e9f3a6ab2714
Source dataset
uspto-grants-1989_06
Patent number
US04839355

Reaction notes

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